CA2770569A1 - Amine-epoxy adducts and their use for preparing polyurea and polyurea-polyurethane coatings - Google Patents
Amine-epoxy adducts and their use for preparing polyurea and polyurea-polyurethane coatings Download PDFInfo
- Publication number
- CA2770569A1 CA2770569A1 CA2770569A CA2770569A CA2770569A1 CA 2770569 A1 CA2770569 A1 CA 2770569A1 CA 2770569 A CA2770569 A CA 2770569A CA 2770569 A CA2770569 A CA 2770569A CA 2770569 A1 CA2770569 A1 CA 2770569A1
- Authority
- CA
- Canada
- Prior art keywords
- amine
- adduct
- epoxy
- adducts
- polymer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000004593 Epoxy Substances 0.000 title claims abstract description 66
- 229920002396 Polyurea Polymers 0.000 title abstract description 40
- 239000011527 polyurethane coating Substances 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 238000006243 chemical reaction Methods 0.000 claims abstract description 35
- 238000002360 preparation method Methods 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 15
- 125000003277 amino group Chemical group 0.000 claims abstract description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 11
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 7
- 230000001476 alcoholic effect Effects 0.000 claims abstract description 4
- 229920000642 polymer Polymers 0.000 claims description 94
- 150000001412 amines Chemical class 0.000 claims description 63
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- 238000000576 coating method Methods 0.000 claims description 46
- 239000000306 component Substances 0.000 claims description 36
- 150000004985 diamines Chemical class 0.000 claims description 20
- 239000003085 diluting agent Substances 0.000 claims description 16
- 125000003700 epoxy group Chemical group 0.000 claims description 15
- 239000011248 coating agent Substances 0.000 claims description 14
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- 231100001261 hazardous Toxicity 0.000 claims description 8
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- 230000007423 decrease Effects 0.000 claims description 5
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229920000768 polyamine Polymers 0.000 claims description 5
- 229920005862 polyol Polymers 0.000 claims description 4
- 150000003077 polyols Chemical class 0.000 claims description 3
- 125000004427 diamine group Chemical group 0.000 claims 1
- HGXVKAPCSIXGAK-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine;4,6-diethyl-2-methylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C(C)=C1N.CCC1=CC(C)=C(N)C(CC)=C1N HGXVKAPCSIXGAK-UHFFFAOYSA-N 0.000 description 18
- 239000012948 isocyanate Substances 0.000 description 17
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- 238000012360 testing method Methods 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000000853 adhesive Substances 0.000 description 12
- 230000001070 adhesive effect Effects 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 12
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 11
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- 238000002156 mixing Methods 0.000 description 10
- 230000009257 reactivity Effects 0.000 description 10
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 9
- 201000006747 infectious mononucleosis Diseases 0.000 description 9
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- 239000000463 material Substances 0.000 description 8
- 150000003335 secondary amines Chemical class 0.000 description 8
- MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 7
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000011022 opal Substances 0.000 description 7
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- 150000003141 primary amines Chemical class 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
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- 231100000331 toxic Toxicity 0.000 description 6
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- QIJIUJYANDSEKG-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-amine Chemical compound CC(C)(C)CC(C)(C)N QIJIUJYANDSEKG-UHFFFAOYSA-N 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
- 229920003344 Epilox® Polymers 0.000 description 5
- FEUISMYEFPANSS-UHFFFAOYSA-N 2-methylcyclohexan-1-amine Chemical compound CC1CCCCC1N FEUISMYEFPANSS-UHFFFAOYSA-N 0.000 description 4
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 4
- 229940072282 cardura Drugs 0.000 description 4
- RUZYUOTYCVRMRZ-UHFFFAOYSA-N doxazosin Chemical compound C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 RUZYUOTYCVRMRZ-UHFFFAOYSA-N 0.000 description 4
- 230000002349 favourable effect Effects 0.000 description 4
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- 230000001105 regulatory effect Effects 0.000 description 4
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- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 4
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- 239000007858 starting material Substances 0.000 description 4
- JCZPOYAMKJFOLA-IMJSIDKUSA-N (3s,4s)-pyrrolidine-3,4-diol Chemical compound O[C@H]1CNC[C@@H]1O JCZPOYAMKJFOLA-IMJSIDKUSA-N 0.000 description 3
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 3
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 3
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
- IGSBHTZEJMPDSZ-UHFFFAOYSA-N 4-[(4-amino-3-methylcyclohexyl)methyl]-2-methylcyclohexan-1-amine Chemical compound C1CC(N)C(C)CC1CC1CC(C)C(N)CC1 IGSBHTZEJMPDSZ-UHFFFAOYSA-N 0.000 description 3
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 description 3
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 3
- 238000005422 blasting Methods 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
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- 238000010438 heat treatment Methods 0.000 description 3
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- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000004922 lacquer Substances 0.000 description 3
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- 238000007039 two-step reaction Methods 0.000 description 3
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- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 2
- ULHFFAFDSSHFDA-UHFFFAOYSA-N 1-amino-2-ethoxybenzene Chemical compound CCOC1=CC=CC=C1N ULHFFAFDSSHFDA-UHFFFAOYSA-N 0.000 description 2
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 2
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 2
- FOYHNROGBXVLLX-UHFFFAOYSA-N 2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1N FOYHNROGBXVLLX-UHFFFAOYSA-N 0.000 description 2
- BBBUAWSVILPJLL-UHFFFAOYSA-N 2-(2-ethylhexoxymethyl)oxirane Chemical compound CCCCC(CC)COCC1CO1 BBBUAWSVILPJLL-UHFFFAOYSA-N 0.000 description 2
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 2
- SYEWHONLFGZGLK-UHFFFAOYSA-N 2-[1,3-bis(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COCC(OCC1OC1)COCC1CO1 SYEWHONLFGZGLK-UHFFFAOYSA-N 0.000 description 2
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 2
- XUSNPFGLKGCWGN-UHFFFAOYSA-N 3-[4-(3-aminopropyl)piperazin-1-yl]propan-1-amine Chemical compound NCCCN1CCN(CCCN)CC1 XUSNPFGLKGCWGN-UHFFFAOYSA-N 0.000 description 2
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 2
- 206010059837 Adhesion Diseases 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 2
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
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- 231100000315 carcinogenic Toxicity 0.000 description 2
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 2
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- 231100000707 mutagenic chemical Toxicity 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- KGHYGBGIWLNFAV-UHFFFAOYSA-N n,n'-ditert-butylethane-1,2-diamine Chemical compound CC(C)(C)NCCNC(C)(C)C KGHYGBGIWLNFAV-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229940117969 neopentyl glycol Drugs 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 150000004995 p-toluidines Chemical class 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000162 poly(ureaurethane) Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007788 roughening Methods 0.000 description 1
- 238000004439 roughness measurement Methods 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical group C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
- C08G18/6415—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63 having nitrogen
- C08G18/643—Reaction products of epoxy resins with at least equivalent amounts of amines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/182—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing using pre-adducts of epoxy compounds with curing agents
- C08G59/184—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing using pre-adducts of epoxy compounds with curing agents with amines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2150/00—Compositions for coatings
- C08G2150/90—Compositions for anticorrosive coatings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Epoxy Resins (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUP0900532 | 2009-08-27 | ||
| HU0900532A HUP0900532D0 (en) | 2009-08-27 | 2009-08-27 | Amine-epoxy appucts and use of them |
| HUP1000390 | 2010-07-22 | ||
| HU1000390A HU228132B1 (hu) | 2010-07-22 | 2010-07-22 | Amin-epoxi adduktok és alkalmazásuk polikarbamid és polikarbamid-poliuretán bevonatok elõállítására |
| PCT/HU2010/000090 WO2011024014A1 (en) | 2009-08-27 | 2010-08-24 | Amine-epoxy adducts and their use for preparing polyurea and polyurea-polyurethane coatings |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2770569A1 true CA2770569A1 (en) | 2011-03-03 |
Family
ID=46565256
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2770569A Abandoned CA2770569A1 (en) | 2009-08-27 | 2010-08-24 | Amine-epoxy adducts and their use for preparing polyurea and polyurea-polyurethane coatings |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20120157620A1 (de) |
| EP (1) | EP2470581B1 (de) |
| KR (1) | KR20120059586A (de) |
| CN (1) | CN102625815A (de) |
| BR (1) | BR112012007898A2 (de) |
| CA (1) | CA2770569A1 (de) |
| ES (1) | ES2511057T3 (de) |
| RU (1) | RU2012109007A (de) |
| WO (1) | WO2011024014A1 (de) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013096635A2 (en) * | 2011-12-22 | 2013-06-27 | Dow Global Technologies Llc | Epoxy elastomer compositions |
| WO2014052319A2 (en) * | 2012-09-28 | 2014-04-03 | Dow Global Technologies Llc | Adduct compositions |
| KR102103396B1 (ko) * | 2012-10-24 | 2020-04-22 | 꽁빠니 제네날 드 에따블리세망 미쉘린 | 금속을 고무에 접착시키기 위한 접착 프라이머로서 특히 유용한 폴리우레아 |
| FR2997079B1 (fr) | 2012-10-24 | 2015-01-23 | Michelin & Cie | Polyamine polyaromatique soufree utilisable pour la synthese de polyuree |
| CA2990400C (en) * | 2015-06-23 | 2023-01-17 | Arkema Inc. | Water soluble polymers and polymeric adducts along with aqueous solutions thereof |
| AU2017285476A1 (en) * | 2016-06-15 | 2019-01-31 | Steed Mifsud Pty Ltd | Glycerol-based epoxy resins |
| KR101955675B1 (ko) * | 2018-04-23 | 2019-03-07 | (주)새론테크 | 수밀성 및 내식성이 향상된 속경화형 폴리우레아 도료 조성물 및 이를 이용한 시공방법 |
| CN109021213B (zh) * | 2018-06-12 | 2020-12-15 | 瑞奇新材料(广州)有限公司 | 一种水性环氧树脂及其制备方法 |
| CN109206574A (zh) * | 2018-06-25 | 2019-01-15 | 青岛海尔股份有限公司 | 多元醇组合物及其制备的聚氨酯硬质泡沫塑料 |
| CN109722148B (zh) * | 2019-01-03 | 2020-12-22 | 珠海市威旗防腐科技股份有限公司 | 一种触变型无溶剂环氧涂料及其制备方法 |
| WO2020227963A1 (en) * | 2019-05-15 | 2020-11-19 | Dow Global Technologies Llc | Two-component adhesive compositions, articles prepared with same and preparation methods thereof |
| EP3969531A4 (de) * | 2019-05-15 | 2022-12-07 | Dow Global Technologies LLC | Zweikomponentige klebstoffzusammensetzungen, damit hergestellte artikel und herstellungsverfahren dafür |
| CN111607065B (zh) * | 2020-06-09 | 2021-11-23 | 中国人民解放军海军勤务学院 | 螺旋桨防污、防腐用两亲性高分子材料及其制备方法 |
| KR102683755B1 (ko) * | 2024-04-12 | 2024-07-16 | 아하방수텍 주식회사 | 준속경 폴리우레아씰, 이를 사용한 도막 복합 시스템 및 방수 공법 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3637902A (en) * | 1969-08-26 | 1972-01-25 | Celanese Coatings Co | Epoxide resins cured with amine-glycidyl ester adducts in admixture with a phenolic accelerator |
| BE857754A (fr) * | 1976-08-18 | 1978-02-13 | Celanese Polymer Special Co | Composition de resine pour revetements, notamment par electrodeposition cathodique |
| DE2735013A1 (de) * | 1977-08-03 | 1979-02-15 | Bayer Ag | Hydroxylgruppen und urethano-aryl- sulfonsaeuregruppenenthaltende verbindungen |
| US4525542A (en) * | 1984-09-20 | 1985-06-25 | Celanese Corporation | Novolac based epoxy resin curing agents for use in solvent |
| GB8530645D0 (en) * | 1985-12-12 | 1986-01-22 | Ici Plc | Coating compositions |
| DE4133517A1 (de) * | 1991-10-10 | 1993-04-15 | Bayer Ag | Hitzehaertbares beschichtungsmittel und seine verwendung |
| DE19520855A1 (de) * | 1995-05-02 | 1996-11-07 | Hoechst Ag | Aliphatische Epoxid-Amin-Addukte mit hoher Seitenkettenverzweigung, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
| US5681907A (en) * | 1996-01-04 | 1997-10-28 | Air Products And Chemicals, Inc. | Fast cure amines for ambient and subambient cure of epoxy resins comprising methylamine adducts |
| US5731397A (en) * | 1996-04-16 | 1998-03-24 | Huntman Petrochemical Corporation | Polyurea spray railcar lining systems |
| US6262186B1 (en) * | 1998-05-11 | 2001-07-17 | Shell Oil Company | Isocyanate-modified epoxy-functional polyester with crosslinking agent |
| MXPA00012660A (es) * | 1998-06-18 | 2003-08-01 | Mackinac Group Inc | METODO PARA AMORTIGUAR EL RUIDO, LA VIBRACION Y LA ASPEREZA DE UN SUBSTRATO Y COMPOSICIoN PARA EL MISMO. |
| CA2438773C (en) * | 2001-02-17 | 2008-12-30 | Hehr International Inc. | Polyurea polymers prepared from polyamine epoxide adduct |
| CN1257206C (zh) * | 2001-08-28 | 2006-05-24 | 荷兰解决方案研究有限公司 | 用于环氧树脂低温固化体系的低粘度固化剂组合物 |
| BRPI0608065B8 (pt) * | 2006-08-09 | 2017-07-04 | Huntsman Petrochemcal Corp | polieteralcanolaminas do tipo pente em tintas e revestimentos |
-
2010
- 2010-08-24 BR BR112012007898A patent/BR112012007898A2/pt not_active IP Right Cessation
- 2010-08-24 CA CA2770569A patent/CA2770569A1/en not_active Abandoned
- 2010-08-24 CN CN2010800381022A patent/CN102625815A/zh active Pending
- 2010-08-24 KR KR1020127007835A patent/KR20120059586A/ko not_active Application Discontinuation
- 2010-08-24 ES ES10757466.7T patent/ES2511057T3/es active Active
- 2010-08-24 US US13/390,263 patent/US20120157620A1/en active Pending
- 2010-08-24 WO PCT/HU2010/000090 patent/WO2011024014A1/en active Application Filing
- 2010-08-24 RU RU2012109007/04A patent/RU2012109007A/ru not_active Application Discontinuation
- 2010-08-24 EP EP10757466.7A patent/EP2470581B1/de not_active Not-in-force
Also Published As
| Publication number | Publication date |
|---|---|
| EP2470581A1 (de) | 2012-07-04 |
| KR20120059586A (ko) | 2012-06-08 |
| EP2470581B1 (de) | 2014-08-13 |
| ES2511057T3 (es) | 2014-10-22 |
| BR112012007898A2 (pt) | 2016-03-22 |
| US20120157620A1 (en) | 2012-06-21 |
| WO2011024014A1 (en) | 2011-03-03 |
| RU2012109007A (ru) | 2013-10-10 |
| CN102625815A (zh) | 2012-08-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20160112 |